Give T.I. $75 Million or He Will Quit

T.I. announced earlier today that he would sign to a label, and his asking price is steep: $75 million. The deal T.I. is proposing, as laid out on TMZ, would include three albums, "10-20 percent of publishing, touring, merchandise, film and TV rights," corporate endorsement deals, and exclusive signing of all artists on his Grand Hustle label.

Although the site claims T.I. finished his 10-year contract with Atlantic last month, HipHopWired has reported that Atlantic Records still claims T.I. as a signnee to the label.

TMZ also reports that Sony offered $50 million, and Universal will be meeting with him later this week. There are also talks that Dr. Dre is trying to woo him to Interscope, and Jay-Z is interested in bringing him aboard at Roc Nation, Jay's venture under the Live Nation umbrella.

Coming fresh off another impressive sales week for Trouble Man: Heavy is the Head (the record has sold 312,000 copies since its December 18 release) T.I. is wisely thinking now is the time to capitalize.

While new artists are signed for comparatively smaller numbers (A$AP Rocky reportedly signed to RCA for $3 million in 2011), there is a history of established legacy artists obtaining seemingly large deals; call them "too big to fail" investments.

In 2007, Madonna signed a reported $120 million deal with Live Nation. The following year, Jay-Z received a $150 million package with the entertainment company, Live Nation's first major foray into hip-hop and another gauntlet thrown in a battle with traditional record labels.

A few things to consider:

These numbers are impressive but they seem so big because they are investments in the artist's entire career: endorsements, touring, merchandise, etc. are all a piece of the puzzle. The idea for companies interested is "diversifying income streams," meaning putting up a lot of money in order to get pieces from each pie.

T.I. is younger than Jay-Z, and the success of his recent album suggest he's proven his long-term viability. He clearly still has a significant following. On the other hand...

He's a career criminal. In 1998, he was arrested for distribution of cocaine, manufacturing and distributing a controlled substance and giving authorities a false name. After serving one year on a three-year sentence, he was again arrested in 2001 for gun possession. 2002, same thing. In 2004, his career was taking off when he was caught again with ammunition, silencers, and photos of him holding weapons. Then came his weapons charge in 2007; after the 2006 shooting death of his friend Philant Johnson, the rapper attempted to illegally purchase firearms and was busted by federal agents. He faced a potentially long prison sentence, but his attorneys managed to bring it down to 366 days.

After making it out and expressing contrition...he was arrested again in 2010 for drug possession.

If anything could hold back investors, it's his seeming inability to stay out of trouble.